Entrepreneur–a big word encompassing many things that often leaves some to wonder what it exactly defines. It is a mindset, an indescribable impulse to create and pursue. It is an ambitious individual, motivated by risk and reward, who cannot fathom following the status quo.
WAVE Advisory Board member, Jeff Kaplan, is the epitome of an entrepreneur.
From a young age, Jeff discovered his entrepreneurial spirit out of necessity, “My mom raised three kids on her own and worked a full-time job as a social worker, needless to say, if we wanted any spending money we needed to hustle for it ourselves.” This sparked the beginning of his entrepreneurial mindset; leading him to grind throughout his adolescence selling newspapers, creating his own landscaping business, and designing and selling tie-dye t-shirts out of his high school locker.
Although starting much smaller than he would end up, Jeff always knew he wanted to start his own business. However, it wasn’t until college that the word ‘entrepreneur’ came into his vocabulary. After attending the University of Wisconsin-Madison School of Business, Jeff graduated with a Bachelor of Business Administration degree double majoring in accounting and marketing with a certificate in international business. To him, learning business principles in the classroom provided the foundation to one day pursue what he really wanted to do with his life: entrepreneurship.
Upon graduation, rather than venture out on his own, Jeff did the exact opposite and went to work for a Fortune 100 company in a rigorous financial management program. “I really wanted to just go for it and start my own business after college; however, I felt I first needed real-world practical experience. Looking back, I still remember my first day of work and feeling physically ill sitting in my car waiting to enter this massive corporate office parking lot. I felt like just another cog in a big machine. I had the moment of, ‘What do I really want to do with my life? What makes me happy? What am I passionate about?’ At the time, the idea of working for a startup where you could innovate, challenge the norm, and move quickly seemed too exciting.”
Against everyone’s advice, Jeff stayed true to his own promise and left his corporate job less than two years in and moved to the West Coast. He joined an early stage software company and took the opportunity to immerse himself in all aspects of the business from sales to product planning and development. “It was exciting. It was fast. I was working 100+ hours a week—all the crazy things you’d hear about startups–but it didn’t feel like work because we were having so much fun growing the business and seeing the results in weeks versus months or years.”
Ironically, Jeff is the first to comment on how the corporate job he dreaded helped him in the startup world, “Working for a big company right out of college prepared me in many ways with the basic tools needed to be a successful operator learning how to analyze data, build models, communicate, and properly present.” To this day, he still leverages these skills more than two decades removed.
After starting, building, and selling several companies in the data mining space over the past 25 years, Jeff is now settled in the Greater Chicago area working as the Chief Operating Officer at Tock (recently acquired by Squarespace). Here he utilizes all he has learned from his past experiences to oversee all aspects of the company’s growth and operations.
As for where he sees himself in the future, “I still love being an operator, building products that provide real value to our customers and in turn creating jobs for the next generation of entrepreneurs. I’ve also entered a new phase in my career where I can dedicate more of my time investing in early stage companies, serving on boards, and mentoring others. Who knows, maybe one day I’ll get the itch again to start another company.”
Becoming a part of the WAVE Advisory Board was easy for Jeff. His true passion is creating and being involved in the Weinert Center has given him the ability to work with new entrepreneurs, learn more about new businesses, and stay up-to-date on emerging technologies.
Most importantly, Jeff loves the ability to pay it forward. Although an entrepreneur at heart, it’s his entrepreneurial mindset that has set him apart. He wants to mentor others and see young entrepreneurs successfully carry out their own dreams.
Welcome to the WAVE Advisory Board Jeff!